In this episode of the Collective Genius Podcast, I sit down with Ryan Haywood—longtime CG member, real estate investor, and author of From Commission to Capital—for one of the most personal and relatable conversations we’ve had on this show. Ryan shares how he went from managing Foot Locker stores and running a collections call center to closing 115 wholesale deals in his very first year of real estate, all out of Saint Joseph, Missouri.

But this isn’t just a story about scaling up. It’s about scaling right. Ryan opens up about the moment he realized chasing bigger numbers was pulling him away from the life he actually wanted—and how he made the hard decision to step back, hire a CEO, and build a business that finally matched his why. From building a rental portfolio to doing strategic flips with a two-person team, Ryan’s story is a reminder that success looks different for everyone—and finding your version of it is the whole point.

Timeline Summary

[1:30] – Welcome and intro to Ryan Haywood from Saint Joseph, Missouri

[3:30] – The common thread among real estate investors: the drive to build something

[4:10] – Where Ryan’s business stands today: wholesaling, rentals, and flips with a lean team

[6:25] – Why you can’t reach true clarity without a deeply defined “why”

[8:47] – How CG first heard about Ryan through David Leko and Deal Machine

[10:05] – Ryan’s pre-real estate career: Foot Locker, collections call centers, and fiber optic sales

[12:14] – The moment corporate paycheck manipulation pushed him toward entrepreneurship

[15:04] – Walking away from the W-2 world with a baby on the way and no roadmap

[15:58] – Halloween 2019: Megan finds a Facebook post about wholesaling and everything changes

[17:01] – Max Maxwell’s 30-day wholesaling challenge and Ryan’s first deal in 14 days

[18:11] – First month doing seven deals; six close at a live event and change his life

[19:38] – Hitting 115 deals in year one and starting to feel alone at the top

[20:02] – The dark, lonely feeling that led Ryan to finally take the call with CG

[21:19] – Ryan’s skepticism about joining a mastermind and Megan closing the deal

[23:57] – Anxiety walking into his first CG event—and deciding to do a magic trick

[26:52] – Going first in the presentations, killing it, and Ren Bartlett texting mid-talk

[29:08] – Why even introverted entrepreneurs find their tribe inside CG

[29:29] – Conversations about scaling into new markets and the pressure to go bigger

[30:39] – The turning point: realizing scale was costing him the life he built the business for

[32:09] – Stepping back, building a rental portfolio, and finding the right rhythm

[33:38] – Finding CEO Clint through CG and the transformation that followed

[37:05] – Using a lean, high-trust team to free up time for bigger opportunities

[40:14] – Why Ryan wrote From Commission to Capital and what it’s really about

[44:20] – Where to find the book and how to follow Ryan

5 Key Takeaways

1. Know Your Why Before You Scale – Ryan’s biggest pivot came from realizing the business had outgrown the life he actually wanted. A clearly defined why is the only thing that keeps you anchored.
2. Scaling Back Can Be the Smartest Move – Doing fewer deals with a smaller team isn’t failure. For Ryan, it was the path to profitability, presence, and peace of mind.
3. The Right Hire Changes Everything – Bringing on CEO Clint gave Ryan the ability to step back from day-to-day operations without the business missing a beat.
4. Build a Portfolio While You Wholesale – The CG community pushed Ryan to buy deals instead of just flipping them. That rental portfolio became the foundation for long-term financial freedom.
5. Community Accelerates Clarity – Ryan credits Collective Genius not just for deal strategies, but for helping him see when to push and when to pull back.

Links & Resources

• From Commission to Capital by Ryan Haywood – Available on Amazon (look for the green shoe on the cover)
• Deal Machine Podcast – Co-hosted with David Leko, available on YouTube and all podcast platforms (500+ episodes)
• Ryan on Instagram: @RJHaywood13
• Heritage Home Investments: @heritage_home_investments on Instagram
• ExploreCG.com – Learn more about the Collective Genius community

If Ryan’s story resonated with you—whether you’re grinding toward your first deal or rethinking what the business you’ve built is actually for—be sure to follow, rate, and review the Collective Genius Podcast. And pass it along to someone who needs a reminder that building the right business matters more than building the biggest one.